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EP3898852B1 - Revêtement protecteur contre les hautes températures à durcissement à température ambiante - Google Patents

Revêtement protecteur contre les hautes températures à durcissement à température ambiante

Info

Publication number
EP3898852B1
EP3898852B1 EP19835764.2A EP19835764A EP3898852B1 EP 3898852 B1 EP3898852 B1 EP 3898852B1 EP 19835764 A EP19835764 A EP 19835764A EP 3898852 B1 EP3898852 B1 EP 3898852B1
Authority
EP
European Patent Office
Prior art keywords
polysiloxane
component
coating composition
substrate
curing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
EP19835764.2A
Other languages
German (de)
English (en)
Other versions
EP3898852A1 (fr
Inventor
Qiang Huang
Dikran BETZIG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
PPG Industries Ohio Inc
Original Assignee
PPG Industries Ohio Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by PPG Industries Ohio Inc filed Critical PPG Industries Ohio Inc
Publication of EP3898852A1 publication Critical patent/EP3898852A1/fr
Application granted granted Critical
Publication of EP3898852B1 publication Critical patent/EP3898852B1/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/38—Boron-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/08—Anti-corrosive paints
    • C09D5/082—Anti-corrosive paints characterised by the anti-corrosive pigment
    • C09D5/084—Inorganic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2217—Oxides; Hydroxides of metals of magnesium
    • C08K2003/222—Magnesia, i.e. magnesium oxide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C08K2003/328—Phosphates of heavy metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group

Definitions

  • the present invention relates to silicone coating compositions, coatings formed therefrom, and methods of forming such coatings.
  • Silicone polymers have been used in corrosion resistance coatings.
  • US 2018/0334587 A1 and WO 2014/164202 A1 describe anticorrosive epoxy siloxane coating compositions.
  • Such silicone polymers typically are applied to a substrate, air dried, and then cured at elevated temperatures of 175-200°C (350-400°F). During use at temperatures above 350°C (660°F) such coatings tend to become porous, thereby reducing their protective effect on the substrate.
  • the present invention comprises an ambient curable coating composition comprising a mixture of components comprising (a) a polysiloxane having a Mw of at least 20,000 as determined by gel permeation chromatography, (b) an alkoxy polysiloxane, and (c) an inorganic corrosion inhibitor; a method of preparing a coating comprising (i) applying the coating composition to a substrate and (ii) curing component (b) at ambient conditions; and a substrate at least partially coated with the coating composition.
  • Fig. 1 is a set of photographs of the coated panels tested in Examples 1-10.
  • any numerical range recited herein is intended to include all sub-ranges subsumed therein.
  • a range of "1 to 10" is intended to include all sub-ranges between (and including) the recited minimum value of 1 and the recited maximum value of 10, that is, having a minimum value equal to or greater than 1 and a maximum value of equal to or less than 10.
  • the transitional term “comprising” (and other comparable terms, e.g., “containing” and “including”) is “open-ended” and open to the inclusion of unspecified matter. Although described in terms of “comprising”, the terms “consisting essentially of” and “consisting of” are also within the scope of the invention.
  • the silicone coating composition of the present invention is curable at ambient conditions, e.g. at ambient temperature, such as in the range of 2-60°C (including room temperature, e.g. 20-25°C) and relative humidity in the range of 1-100%.
  • the ambient curable coating composition includes (a) a polysiloxane having a molecular weight (Mw) of at least 20,000 or at least 100,000 or at least 200,000 (all Mw disclosed herein being determined by gel permeation chromatography using a polystyrene standard for calibration), (b) an alkoxy polysiloxane and (c) an inorganic corrosion inhibitor, as well as an optional curing agent.
  • Mw molecular weight
  • the polysiloxane (a) having a Mw of at least 20,000 or at least 100,000 or at least 200,000 may be referred to herein relative to other polymeric components as a "high Mw polysiloxane".
  • Suitable polysiloxanes have the formula (I): where each R 1 is independently a hydroxy group or an alkyl, aryl, or alkoxy group having up to six carbon atoms, and where n is selected so that the molecular weight for the polysiloxane is at least 10,000.
  • Such high Mw polysiloxanes are commercially available, such as SILRES REN 50, SILRES REN 60, and SILRES REN 80 from Wacker Chemical Corporation (Adrian, MI) or DOWSII, RSN-0805, DOWSII, RSN-0806, and DOWSIL RSN-0808 from Dow Chemical Company (Midland, MI) or SILIKOPHEN P50/X and SILIKOPHEN P80/X from Evonik Corporation (Parsippany, NJ).
  • SILRES REN 50, SILRES REN 60, and SILRES REN 80 from Wacker Chemical Corporation (Adrian, MI) or DOWSII, RSN-0805, DOWSII, RSN-0806, and DOWSIL RSN-0808 from Dow Chemical Company (Midland, MI) or SILIKOPHEN P50/X and SILIKOPHEN P80/X from Evonik Corporation (Parsippany, NJ).
  • the alkoxy polysiloxane (b) used in the present invention includes polysiloxanes different from the polysiloxane (a) and having the general formula (II): where each R 2 group may be hydrogen, alkyl, or alkoxy, and each R 3 group may be alkoxy or acetoxy, each of R 2 and R 3 having up to six carbon atoms, where m is selected so that the molecular weight for the alkoxy polysiloxane is up to 8,000.
  • Such alkoxy polysiloxanes are commercially available, such as SILRES MSE 100 from Wacker Chemical Corporation (Adrian, MI) and DOWSIL 2403 from Dow Chemical Company (Midland, MI).
  • the R 2 group may be a methyl group of a methoxy functional methyl polysiloxane.
  • the alkoxy polysiloxane is moisture curable, meaning that it is further polymerized and/or crosslinked in the presence of moisture that is available in the surrounding atmosphere.
  • the polysiloxane is further polymerized and/or crosslinked, typically using water that is available in the surrounding atmosphere (i.e. as moisture), and present within the curable coating composition. Water hydrolyzes alkoxy groups on the polysiloxane, resulting in free hydroxyl groups. In a subsequent condensation reaction between the free hydroxyl groups, the polysiloxane is considered to be cured.
  • This reaction mechanism may be described as a hydrolysis-condensation mechanism, with the reactions typically catalyzed with an alkyl titanate (hydrolysis reaction) and a strong base (condensation reaction).
  • the coating composition of the present invention includes an inorganic corrosion inhibitor such as magnesium oxide, zinc phosphate, metal-modified zinc phosphates, metal-modified phosphosilicate and/or metal-modified borosilicate, wherein the metal comprises calcium, barium, strontium, molybdenum, magnesium, and/or aluminum and "metal-modified” refers to metal additives included therewith.
  • corrosion inhibitor it is meant a component that improves corrosion resistance, i.e. the resistance of the coating against reaction with or other degradation by adverse conditions in the surrounding environment, of an underlying substrate as compared to the same coating composition except not containing the corrosion inhibitor.
  • the curing agent may comprise an organometallic compound such as alkyl titanate, e.g. tetra-n-butyl titanate, acids (such as sulphonic, phosphoric, boric acids), zinc compounds, acetyl acetonate and various other basic compounds.
  • organometallic compound such as alkyl titanate, e.g. tetra-n-butyl titanate, acids (such as sulphonic, phosphoric, boric acids), zinc compounds, acetyl acetonate and various other basic compounds.
  • the polysiloxane (a) may be present in the coating composition (with all references to percentages herein based on the entire coating composition, including solvent, in a ready-to-use form) in an amount of 1 weight (wt.) % or greater, or 2 wt. % or greater or may be present at 20 wt. % or less, or 5 wt. % or less, or 12 wt. % or less.
  • the polysiloxane (a) may be present in the coating composition in a wt. % range of from 1-20, such as 2-15 or 2-12 or another range in combination using these endpoints.
  • the alkoxy polysiloxane (b) maybe present in the coating composition in an amount of 2 wt.
  • the high Mw polysiloxane, alkoxy polysiloxane, and inorganic corrosion inhibitor form a protective organometallic coating on the substrate.
  • a person skilled in the art working the present invention will know that the selection of the particular compounds for each of (a) a polysiloxane having a Mw of at least 20,000 as determined by gel permeation chromatography, (b) an alkoxy polysiloxane, and (c) an inorganic corrosion inhibitor will depend on the particular application of the coating composition.
  • the coating composition, once applied to the at least one surface of the substrate may be allowed to cure at ambient conditions until fully cured or, alternatively, may be cured at an elevated temperature, from above ambient temperature up to 150°C-200°C, for example, by placing the coated substrate in a drying or curing oven.
  • the substrate may be removed from the oven after complete curing of the coating composition or after partial curing of the coating composition, after which the coating composition may continue to cure on the substrate at ambient temperature until complete cure is attained.
  • Clause five is directed to the coating composition of any of clauses one to four, wherein component (a) comprises an alkyl aryl polysiloxane.
  • Clause six is directed to the coating composition of any of clauses one to five, wherein component (b) comprises an alkoxy functional alkyl polysiloxane.
  • Clause seven is directed to the coating composition of any of clauses one to six, wherein the inorganic corrosion inhibitor (c) comprises magnesium oxide, zinc phosphate, metal-modified zinc phosphates, metal-modified phosphosilicate and/or metal-modified borosilicate, wherein the metal comprises calcium, barium, strontium, molybdenum, magnesium, and/or aluminum.
  • Clause eight is directed to a method of preparing a coating comprising: (i) applying the coating composition of any of clauses one to seven to a substrate; and (ii) curing component (b) at ambient conditions.
  • Clause nine is directed to the method of clause eight, further comprising prior to step (i) preparing a mixture of reactants comprising a first component comprising the polysiloxane (a) and the alkoxy functional polysiloxane (b) and a second component comprising the inorganic corrosion inhibitor (c); and mixing the first and second components.
  • Clause ten is directed to the method of clauses eight or nine, wherein the second component further comprises additional polysiloxane (a).
  • Clause sixteen is directed to the coating composition of any of clauses one to seven wherein the polysiloxane (a) is present in an amount by weight of 1-20% or 2-15% or 2-12%.
  • Clause seventeen is directed to the coating composition of any of clauses one to seven, sixteen, or seventeen, wherein the inorganic corrosion inhibitor is preset in an amount by weight of 1-35% or 2-25% or 4-20%.
  • Clause nineteen is directed to the coating composition of any of clauses one to seven or sixteen to eighteen, further comprising a curing agent for moisture curing alkoxy polysiloxane (b) in an amount by weight of 0.05-5 or 0.1-3 or 0.2-2.
  • Part A Part B with titanate only
  • Example 1-8 two parts A were mixed with one part B (by volume) with a mechanical agitator.
  • Example 9 also two component system
  • 93.3 parts A were mixed with one part B (by volume) with a mechanical agitator.
  • Example 10 one component system
  • All items were mixed with a mechanical agitation.
  • the mixtures in Examples 1-10 were each applied direct to metal on carbon steel panels using a HVLP air spray gun with tip opening of 1.7 mm to produce coatings at ambient conditions on the panels at 10-12 mils of dry film thickness.
  • Accelerated Thermal Cyclic Corrosion Test The accelerated thermal cyclic corrosion test method used a programmable oven and a salt fog chamber based on ASTM B117 salt fog test.
  • the B117 salt fog test is an ASTM standardized corrosion test method, used to check corrosion resistance of materials and surface coatings. It is an accelerated corrosion test that produces a corrosive attack to coated samples in order to evaluate the suitability of the coating for use as a protective finish.
  • the appearance of corrosion products (rust or other oxides) is evaluated after a pre-determined period of time. Test duration depends on the corrosion resistance of the coating; generally, the more corrosion resistant the coating is, the longer the period of testing before the appearance of corrosion/rust.
  • the test included intermittent salt fog exposure post thermal cyclic load. Each cycle included 3 days dry heat cyclic exposure from ambient to 800°F (427°C). Panels were quenched in cold water at the end of each day during dry cycle. After 3 days dry cycle, panels were placed in a B117 salt spray chamber for 3 days. Panels were inspected after each cycle (rust rating per ASTM D610 and blistering/cracking ratings per ASTM D1654-08). The test duration continued until there was an appearance of blistering/cracking/delaminating, corrosion, and/or rust. A higher number of cycles before such deterioration is indicative of improved corrosion resistance. Pull off adhesion and heat resistance were tested according to ASTM D4541-17 and ASTM 2485-18, respectively.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Claims (15)

  1. Composition de revêtement durcissable à température ambiante, définie comme une température dans la plage de 2 à 60 °C et une humidité relative dans la plage de 1 à 100 %, comprenant un mélange de constituants comprenant :
    (a) un polysiloxane ayant un Mw d'au moins 20 000 tel que déterminé par chromatographie par perméation de gel en utilisant un standard de polystyrène ;
    (b) un polysiloxane à fonction alcoxy ; et
    (c) un inhibiteur de corrosion inorganique.
  2. Composition de revêtement selon la revendication 1, comprenant en outre un agent de durcissement pour durcir le constituant (b) par durcissement à l'humidité.
  3. Composition de revêtement selon la revendication 1, dans laquelle le Mw du constituant (a) est d'au moins 100 000.
  4. Composition de revêtement selon la revendication 1, dans laquelle le Mw du constituant (a) est d'au moins 200 000.
  5. Composition de revêtement selon la revendication 1, dans laquelle le constituant (a) comprend un alkyl aryl polysiloxane.
  6. Composition de revêtement selon la revendication 1, dans laquelle le constituant (b) comprend un alkyl polysiloxane à fonction alcoxy.
  7. Composition de revêtement selon la revendication 1, dans laquelle l'inhibiteur de corrosion inorganique (c) comprend de l'oxyde de magnésium, du phosphate de zinc, des phosphates de zinc modifiés par du métal, du phosphosilicate modifié par du métal et/ou du borosilicate modifié par du métal, dans laquelle le métal comprend du calcium, du baryum, du strontium, du molybdène, du magnésium et/ou de l'aluminium.
  8. Procédé de préparation d'un revêtement comprenant :
    (i) l'application de la composition de revêtement selon la revendication 1 sur un substrat ; et
    (ii) le durcissement du constituant (b) dans des conditions ambiantes.
  9. Procédé selon la revendication 8, comprenant en outre la préparation d'un mélange de réactifs comprenant un premier constituant comprenant le polysiloxane (a) et le polysiloxane à fonction alcoxy (b) et un second constituant comprenant l'inhibiteur de corrosion inorganique (c) ; et le mélange des premier et second constituants.
  10. Procédé selon la revendication 9, dans lequel le second constituant comprend en outre du polysiloxane (a) supplémentaire.
  11. Procédé selon la revendication 8, comprenant en outre une étape supplémentaire (iii) de durcissement du constituant polysiloxane à fonction alcoxy (b) à une température d'au moins 93 °C (200 °F).
  12. Substrat au moins partiellement revêtu de la composition de revêtement selon la revendication 1.
  13. Substrat selon la revendication 12, dans lequel le substrat est un métal.
  14. Élément de traitement industriel comprenant le substrat selon la revendication 13.
  15. Élément de traitement industriel selon la revendication 14, dans lequel l'élément comprend un réacteur, une cheminée d'échappement, un reformeur, une colonne de distillation, une tuyauterie, une vanne, un échange de chaleur, une chaudière ou un réservoir de stockage, ou un moteur d'avion.
EP19835764.2A 2018-12-19 2019-12-17 Revêtement protecteur contre les hautes températures à durcissement à température ambiante Active EP3898852B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201862781636P 2018-12-19 2018-12-19
PCT/IB2019/060880 WO2020128805A1 (fr) 2018-12-19 2019-12-17 Revêtement protecteur contre les hautes températures à durcissement à température ambiante

Publications (2)

Publication Number Publication Date
EP3898852A1 EP3898852A1 (fr) 2021-10-27
EP3898852B1 true EP3898852B1 (fr) 2025-08-13

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EP19835764.2A Active EP3898852B1 (fr) 2018-12-19 2019-12-17 Revêtement protecteur contre les hautes températures à durcissement à température ambiante

Country Status (11)

Country Link
US (2) US12359088B2 (fr)
EP (1) EP3898852B1 (fr)
JP (1) JP2022515399A (fr)
KR (1) KR20210095656A (fr)
CN (1) CN113195649A (fr)
DK (1) DK3898852T3 (fr)
ES (1) ES3039272T3 (fr)
MX (2) MX2021007493A (fr)
PL (1) PL3898852T3 (fr)
SG (1) SG11202106448SA (fr)
WO (1) WO2020128805A1 (fr)

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WO2022045045A1 (fr) * 2020-08-28 2022-03-03 中国塗料株式会社 Composition de peinture, film de revêtement, matériau de base ayant un film de revêtement et méthode de fabrication associée
CN112960939A (zh) * 2021-02-07 2021-06-15 枣阳市锦烨节能建材有限公司 一种彩色沥青混凝土及其制备方法

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KR20180012177A (ko) 2016-07-26 2018-02-05 한국파렛트풀(주) 자연 경화형 내열도료 및 이를 이용한 컨테이너
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JP7089938B2 (ja) 2017-06-23 2022-06-23 中国塗料株式会社 耐熱塗料組成物、耐熱塗膜、耐熱塗膜付き基材およびその製造方法

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MX2021007493A (es) 2021-08-05
DK3898852T3 (en) 2025-09-01
PL3898852T3 (pl) 2025-09-22
US12359088B2 (en) 2025-07-15
US20220135837A1 (en) 2022-05-05
KR20210095656A (ko) 2021-08-02
MX2025012387A (es) 2025-11-03
CN113195649A (zh) 2021-07-30
ES3039272T3 (en) 2025-10-20
EP3898852A1 (fr) 2021-10-27
US20250346781A1 (en) 2025-11-13
JP2022515399A (ja) 2022-02-18

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